Your story sound similar to mine, only that I could cash out some of my shares when a PE company took over, so I don't lose everything. I had to roll over some of my shares though, and these are close to worthless now. It's still painful getting more and more diluted in extreme down rounds, as business is running out of cash and debt is too high.
From my experience, it's inevitable that you will get diluted, you can't change that. It also does not matter what you have done for the business before, the investor persons won't care. What matters is the now and the future.
So focus on the future. You should align your salary and package with that of the COO. Your new shares could also have similar conditions as the new investor will etc. Discuss it with your current investors and the new ones. They don't want to write off their investment too, and certainly want to keep you on board?
I don't understand your fear that they will fire you? You will still keep your shares, and are free to do something new (and will probably earn much more).
You can only change the future. You seem to be a technical person (nothing wrong about that, I'm too :-)), a business person would have negotiated this a long time ago already, and multiple times.
I can feel with you.
Your story sound similar to mine, only that I could cash out some of my shares when a PE company took over, so I don't lose everything. I had to roll over some of my shares though, and these are close to worthless now. It's still painful getting more and more diluted in extreme down rounds, as business is running out of cash and debt is too high.
From my experience, it's inevitable that you will get diluted, you can't change that. It also does not matter what you have done for the business before, the investor persons won't care. What matters is the now and the future.
So focus on the future. You should align your salary and package with that of the COO. Your new shares could also have similar conditions as the new investor will etc. Discuss it with your current investors and the new ones. They don't want to write off their investment too, and certainly want to keep you on board?
I don't understand your fear that they will fire you? You will still keep your shares, and are free to do something new (and will probably earn much more).
You can only change the future. You seem to be a technical person (nothing wrong about that, I'm too :-)), a business person would have negotiated this a long time ago already, and multiple times.